The art collection of the gallery was first exhibited on August 6, 1944 at the History Museum of Kyustendil. It featured artworks by several artists from Kyustendil and 50 paintings by Maystora taken from the Ministry of Education. On May 24, 1959 a City Art Gallery was inaugurated in the reconstructed Synagogue. The Art Gallery has borne the name of Vladimir Dimitrov – Maystora since 1961. His artworks are closely connected with the people from Kyustendil region – he lived and painted in the village of Shishkovtsi for many years.The modern building of the Art Gallery was constructed in 1972 and it is one of the largest in Bulgaria. It possesses the biggest and most significant collection of artworks by Vladimir Dimitrov – Maystora – oil paintings, aquarelles, inks and drawings (1359 pieces). The richest and most varied collection in the Art Gallery’s fund is the one consisting of artworks by artists from Kyustendil, some of them being the most distinguished names in Bulgarian fine art. Since the beginning of the 20th century until today, the Kyustendil Fine Arts School has comprised about 200 authors.